scholarly journals Bisindole Alkaloids from the Alstonia Species: Recent Isolation, Bioactivity, Biosynthesis, and Synthesis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3459
Author(s):  
Kamal P. Pandey ◽  
Md Toufiqur Rahman ◽  
James M. Cook
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Drug Targets ◽  
Partial Synthesis ◽  
Formal Synthesis ◽  
Methyl Substitution ◽  
Synthetic Derivatives

Bisindoles are structurally complex dimers and are intriguing targets for partial and total synthesis. They exhibit stronger biological activity than their corresponding monomeric units. Alkaloids, including those containing C-19 methyl-substitution in their monomeric units, their synthetic derivatives, and their mismatched pairs can be attractive targets for synthesis and may unlock better drug targets. We herein discuss the isolation of bisindoles from various Alstonia species, their bioactivity, putative biosynthesis, and synthesis. The total synthesis of macralstonidine, macralstonine, O-acetylmacralstonine, and dispegatrine, as well as the partial synthesis of alstonisidine, villalstonine, and macrocarpamine are also discussed in this review. The completion of the total synthesis of pleiocarpamine by Sato et al. completes the formal synthesis of the latter two bisindoles.

Studies Towards the Synthesis of (+)- and (–)-Anisomycin and Their Analogues

Synthesis ◽  
2017 ◽  
Vol 50 (01) ◽  
pp. 17-34 ◽  
Author(s):  
Arun Shaw ◽  
Sama Ajay
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Present Review ◽  
Formal Synthesis ◽  
Total Syntheses ◽  
Synthetic Approaches

Anisomycin shows potent biological activity and it has attracted much attention since its isolation in 1954, with around 13 total syntheses and 20 formal syntheses, and also two reports concerning analogues of anisomycin, reported to date. The present review highlights all of these synthetic approaches (around 35) to the total or formal synthesis of anisomycin along with its isomers and analogues.1 Introduction2 Isolation and Therapeutic Importance3 Total Synthesis of (+)-, (–)-, and (±)-Anisomycins and Their Analogues4 Formal Synthesis of (+)- and (–)-Anisomycins and Their Analogues5 Conclusion

Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity

2021 ◽  
Author(s):  
Robert M. Hohlman ◽  
David H. Sherman
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Indole Alkaloids ◽  
Recent Advances

This review covers isolation, biological activity, an overview of total synthesis efforts and recent biosynthetic discoveries related to hapalindole-type indole alkaloids.

Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

2010 ◽  
Vol 51 (2) ◽  
pp. 269-272 ◽  
Author(s):  
Yun-Yee Low ◽  
Kuan-Hon Lim ◽  
Yeun-Mun Choo ◽  
Huey-Shen Pang ◽  
Tadahiro Etoh ◽  
...  
Keyword(s):  
Biological Activity ◽  
Indole Alkaloids ◽  
Partial Synthesis

scholarly journals Total Synthesis of (−)-Vitrenal and Its Biological Activity

1986 ◽  
Vol 59 (6) ◽  
pp. 1897-1900 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Usman S. F. Tambunan ◽  
Tetsuto Tsunoda ◽  
Shô Itô
Keyword(s):  
Biological Activity ◽  
Total Synthesis

Significance of C-terminal cysteine modifications to the biological activity of the Saccharomyces cerevisiae a-factor mating pheromone

1991 ◽  
Vol 11 (7) ◽  
pp. 3603-3612
Author(s):  
S Marcus ◽  
G A Caldwell ◽  
D Miller ◽  
C B Xue ◽  
F Naider ◽  
...  
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Biological Activity ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Biologically Active ◽  
Structural Genes ◽  
Wild Type ◽  
Mating Pheromone ◽  
Carboxy Terminal

We have undertaken total synthesis of the Saccharomyces cerevisiae a-factor (NH2-YIIKGVFWDPAC[S-farnesyl]-COOCH3) and several Cys-12 analogs to determine the significance of S-farnesylation and carboxy-terminal methyl esterification to the biological activity of this lipopeptide mating pheromone. Replacement of either the farnesyl group or the carboxy-terminal methyl ester by a hydrogen atom resulted in marked reduction but not total loss of bioactivity as measured by a variety of assays. Moreover, both the farnesyl and methyl ester groups could be replaced by other substituents to produce biologically active analogs. The bioactivity of a-factor decreased as the number of prenyl units on the cysteine sulfur decreased from three to one, and an a-factor analog having the S-farnesyl group replaced by an S-hexadecanyl group was more active than an S-methyl a-factor analog. Thus, with two types of modifications, a-factor activity increased as the S-alkyl group became bulkier and more hydrophobic. MATa cells having deletions of the a-factor structural genes (mfal1 mfa2 mutants) were capable of mating with either sst2 or wild-type MAT alpha cells in the presence of exogenous a-factor, indicating that it is not absolutely essential for MATa cells to actively produce a-factor in order to mate. Various a-factor analogs were found to partially restore mating to these strains as well, and their relative activities in the mating restoration assay were similar to their activities in the other assays used in this study. Mating was not restored by addition of exogenous a-factor to a cross of a wild-type MAT alpha strain and a MATaste6 mutant, indicating a role of the STE6 gene product in mating in addition to its secretion of a-factor.

Studios on the Total Synthesis of an A7,B7-Dicarbainsulin. III. Assembly of Segments and Generation of Biological Activity

1990 ◽  
Vol 371 (2) ◽  
pp. 1057-1066 ◽  
Author(s):  
Georgi VIDENOV ◽  
Klaus BÜTTNER ◽  
Monika CASARETTO ◽  
Josef FÖHLES ◽  
Hans-Gregor GATTNER ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis

Chemoenzymatic Formal Total Synthesis of Pancratistatin from Narciclasine-Type Compounds via Myers Transposition: Model Study for a Short Conversion of Narciclasine to Pancratistatin

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2896-2900 ◽  
Author(s):  
Ringaile Lapinskaite ◽  
Mukund Ghavre ◽  
Chelsea Rintelmann ◽  
Korey Bedard ◽  
Helen Dela Paz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Recombinant Strain ◽  
Optical Purity ◽  
Allylic Alcohol ◽  
Formal Synthesis ◽  
Toluene Dioxygenase ◽  
Single Isomer ◽  
Model Study ◽  
New Compounds ◽  
Subsequent Opening

A formal total synthesis of pancratistatin was accomplished by conversion of advanced intermediates, used in the synthesis of narciclasine, to pancratistatin precursors via Myers’ reductive transposition as the key strategic step. The synthesis began with the whole cell fermentation of m-dibromobenzene with JM109(pDTG601a), a recombinant strain that over-expresses toluene dioxygenase, which provided the corresponding cis-dihydrodiol 16 as a single isomer with complete optical purity. The key reductive transposition of the allylic alcohol 8a to olefin 9a allowed for further installation of the C-1/C-2 trans-diol, ­required for the pancratistatin scaffold, through the introduction of a cyclic sulfate and its subsequent opening. The formal synthesis of pancratistatin was accomplished in 14 steps (12 operations) from commercially available m-dibromobenzene. Experimental and spectral data are provided for all new compounds.

Sign in / Sign up

Export Citation Format

Share Document